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Thinking Sideways

How to Think Like a Chess Player and Win at Life

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Thinking Sideways

By: Jennifer Shahade
Narrated by: Jennifer Shahade
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Chess is the art of the possible - after all, there are more potential chess games than atoms in the universe.
Great players are experts at exploring options, allowing them to seize an opportunity, idea or move that no one else saw. Two-time US chess champion Jennifer Shahade calls this 'thinking sideways'. And in today's hyper-competitive world, thinking sideways can help you win at life
In Thinking Sideways, Shahade shows you don't have to be a chess player to think more like a chess player. From building mind palaces to crafting decision trees, she reveals the most useful strategies from the ancient game that we can use in our daily lives. Drawing on examples from business, sports and psychology, as well as her own experiences touring the world as a chess and poker champion, Thinking Sideways offers a practical toolkit for smarter thinking and transforms our understanding of what success looks like, and how to achieve it for ourselves.
This book is not about playing chess - it's about how thinking sideways can propel you to success and happiness.©2025 Jennifer Shahade Chess Creativity & Genius Personal Development Personal Success Psychology Psychology & Mental Health Game
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Critic reviews

A masterclass in how to use strategic thinking for critical decision-making and to unlock creative potential. Deeply researched and wonderfully written, full of fascinating insights. (Ken Rogoff, former IMF chief economist, chess Grandmaster, and author of OUR DOLLAR, YOUR PROBLEM)
Thinking Sideways is a must-read book that will teach you how to think and help you succeed at life. (Greg Karber, author of the MURDLE series)
Jennifer Shahade is a brilliant, insightful thinker who never fails to entertain and engage. I'm always amazed by the novel approach she's able to bring to any intellectual challenge and discussion. (Maria Konnikova, author of THE BIGGEST BLUFF and THE CONFIDENCE GAME)
Relatable and highly engaging. Jennifer is a great storyteller with an effortless ability to weave in science, facts and insights. You don't need to know anything about chess to love this book (Alex O’Brien, author of THE TRUTH DETECTIVE and vice-chair of the Association of British Science Writers)
These are lessons not just for chess players, but for all of us. Jen shows how sideways thinking opens up the world. (Carissa Yip, US Women’s Chess Champion and International Master)
Thinking Sideways is brilliant and persuasive: a book I've always wanted to write but Jennifer has done it perfectly. A tour de force/masterpiece. (Bruce Pandolfini, US Chess Hall of Famer, author, and consultant for the Queen’s Gambit)
All stars
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Sometimes the content was v random and not relevant to the topic. I found the intonation of the soft voice really difficult to hear.

Ok but not amazing

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I love Jennifer's style and after listening to Chess Queen multiple times i pre-ordered this and forgot about it. But once it dropped i listened immediately and i'm so glad i did.
It's not usually the kind of book i'll buy to but i took so much away from it i'm sure i'll listen to it again and take away even more. Highly recommended.

Fascinating. I will listen to this again.

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A complete guide into how to focus the mind and make better decisions in life. Each chapter has research, anecdotes, history and how this translates to your life. The secrets of a chess player's mind broken down with fascinating insights. Mindpalaces, memory, art, poker, cheating... hooked from beginning to end! If you want to refine your thinking this book is a must read. A rollercoaster from beginning to end!

Engaging & fascinating insights into the mind of a chess player

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Listened to this after seeing it mentioned a number of times recently and hearing really positive reviews. But I just don’t get the hype and really struggled to get through it. Kept thinking I was missing some key insight, and maybe I am, but honestly I found it really disappointing. Smacks of someone trying to monetise a growing interest in the game in recent years by slapping supposed “life advice” around a chess board.

The stories don’t connect, the supposed goals in each chapter feel like they have been plucked out of their air and a chess story strapped to them, the personal stories are tenuous, the analogies are often a stretch, i just didn’t get where she was going most of the time.

In addition, I found the reading style to be quite annoying. Unnecessary pauses in sentences, odd intonation. An annoying listen.

Others seem to love this book but I’d recommend Range by David Epstein over this every day and Thinking in Bets by Annie Duke is a far superior read.

Disappointing. Not sure what the fuss is about

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